- Covered Up: "And I Love You So" is one of his songs, but has been covered by Elvis and was a hit for Perry Como. In reverse, McLean's "Crying," a huge hit, was originally performed by Roy Orbison.
- Everyone Is Jesus in Purgatory: "American Pie" is about the plane crash that killed Buddy Holly, Ritchie Valens, and The Big Bopper. That much has been confirmed. The rest of the lyrics have been much-discussed as being an extended metaphor about the evolution of Rock, with many guesses as to the identities of the names and places. The King (Elvis Presley), The Jester (Bob Dylan) and The Marching Band (The Beatles) were widely agreed-upon, but McLean Jossed all those in 2022 in the Paramount+ documentary The Day the Music Died: The Story of Don McLean's American Pie;note many of the others are still disputed. Reportedly, years prior to said documentary, when McLean himself was asked about it, he replied "What is the meaning of 'American Pie'? It means I never have to work again."
- Funny Moments: If one doesn't pay attention to the disputed symbolism and takes the lyrics literally, what happens with the Jester in "American Pie" can come off as a Brick Joke. First he steals the King's crown while performing for him, the court failing to convict him for it... then a verse later, during a football game, the same Jester is on the sidelines in a cast. Apparently he didn't get away with the theft as much as he thought.
- Genius Bonus: Several. "American Pie" contains references to events and people who were notable in McLean's childhood. Furthermore, "the Levee" is not a levee, but a bar (giving the phrase "but the Levee was dry" an entirely new meaning).
- Germans Love David Hasselhoff - "Crying" and "Vincent" did much better in the UK, both reaching #1 (in fact they did better than "American Pie" which reached #2). The parent album of "Crying", Chain Lightning, was released in Europe almost three years before it came out in America, and it was the #1 success of "Crying" in the UK that prompted the song and album to finally get an American release.
- Nightmare Fuel: The penultimate verse of "American Pie" obliquely but hauntingly references the murder of Meredith Hunter at a The Rolling Stones concert, with the narrator saying "[he] saw Satan laughing with delight" at the killing.
- Parody Displacement: His kids were such big fans of "Weird Al" Yankovic and have played "The Saga Begins" so much, that even Don has mixed up some of the lyrics of "American Pie" with the parody while performing it.
- Refrain from Assuming:
- There are some people who know "American Pie" as "The Day the Music Died".
- Also, the song "Vincent" is not "Starry Starry Night".
- Second Verse Curse: Because "American Pie" was so long, it was released originally on a dual-sided single. Some radios only played Part One.
- Signature Song: "American Pie", a melancholic masterpiece explaining the history of rock-n-roll ever since the deaths of Buddy Holly, Ritchie Valens and The Big Bopper with tons of metaphors and comparisons for anyone to ponder over and make comparisons to real life events.
- Tough Act to Follow: American Pie was a commercial and critical success, but he never managed to duplicate it.
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